Hydrochloric Acid → (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidine

HRID 568272ノート

反応式

HRID 568272 の反応式
Cl.[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH:13]([OH:22])[C:14]2[S:18][C:17]3=[CH:19][N:20]=[CH:21][N:16]3[CH:15]=2)[CH2:11][C@@H:10]([O:23][Si](C(C)(C)C)(C)C)[CH2:9]1)=[O:7])[CH:3]=[CH2:4].C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)(=O)C.O>[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH:13]([OH:22])[C:14]2[S:18][C:17]3=[CH:19][N:20]=[CH:21][N:16]3[CH:15]=2)[CH2:11][C@@H:10]([OH:23])[CH2:9]1)=[O:7])[CH:3]=[CH2:4]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20639576(3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidine

生成物 1

HCID 70221509(3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidine

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Concentrated hydrochloric acid (0.85 ml) is added dropwise to a solution of 899 mg of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidine in 20 ml of dry acetonitrile under ice cooling, and the mixture is stirred at that temperature for 20 min. The reaction solution is diluted with 50 ml of ethyl acetate, water is added thereto, and the mixture is rendered weakly alkaline by addition of a saturated aqueous sodium hydrogencarbonate solution. The mixture is then extracted three times with ethyl acetate, and the organic layer is washed twice with saturated saline, dried over anhydrous magnesium sulfate and filtered. The solvent is removed by evaporation under reduced pressure to give a crude product of (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidine. Triethylamine (0.46 ml) and 0.24 ml of methanesulfonyl chloride are successively added to a solution of this compound in 20 ml of THF, and the mixture is stirred under an argon stream at −14° C. for 50 min. Water is added to the reaction solution, and the mixture is extracted four times with ethyl acetate. The organic layer is washed once with saturated saline, dried over anhydrous magnesium sulfate and filtered, and the solvent is removed by evaporation under reduced pressure to give a crude product which is then purified by column chromatography on silica gel (ethyl acetate:methanol=9:1) to give 472.6 mg of (3R,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-2-yl)methyl]-3-methanesulfonyloxypyrrolidine (a diastereomer mixture) as a yellow viscous material.

後処理

  1. additionis added
  2. extractionThe mixture is then extracted three times with ethyl acetate
  3. washthe organic layer is washed twice with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent is removed by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-04083ceeaaf946bea7b5a5e66e2a4e1e
出典データセット
uspto-grants-2001_01
特許番号
US06180622B2

反応ノート

読み込み中…